CN113896633B - Preparation method of 3-alkoxy acrylic ester - Google Patents

Preparation method of 3-alkoxy acrylic ester Download PDF

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CN113896633B
CN113896633B CN202010573404.5A CN202010573404A CN113896633B CN 113896633 B CN113896633 B CN 113896633B CN 202010573404 A CN202010573404 A CN 202010573404A CN 113896633 B CN113896633 B CN 113896633B
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CN113896633A (en
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Angie Shanghai Environmental Protection New Material Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention relates to a preparation method of 3-alkoxy acrylic ester, which comprises the steps of introducing carbon monoxide into metal alkoxide solution of ester, and preserving heat until the reaction is complete; then evaporating excessive ester, dripping alcohol solution of hydrogen chloride, after heat preservation reaction is completed, obtaining 3, 3-dialkoxy propionate through aftertreatment, then adding catalyst, and obtaining 3-alkoxy acrylate through reduced pressure distillation after cracking reaction.

Description

Preparation method of 3-alkoxy acrylic ester
Technical Field
The invention belongs to the field of chemistry, and particularly relates to a preparation method of 3-alkoxy acrylic ester.
Background
3-Alkoxy acrylates are an important class of organic compounds, particularly useful in pharmaceutical chemistry, for example for the synthesis of ceftibuten (Ceftibuten). In addition, 3-alkoxy acrylates are important building blocks, which are frequently involved in organic synthesis.
The general method for the synthesis of 3-alkoxy acrylates is the addition reaction of the propiolates with the corresponding alcohols, the reaction conditions reported so far being the addition of relatively large amounts of solvents (generally dichloromethane and ethers), usually using stoichiometric amounts of organic bases as catalysts.
The use of large amounts of solvents and catalysts not only increases the cost, but also the solvents and catalysts themselves are toxic or flammable, which limits the industrialization of the process.
Disclosure of Invention
1. Technical problem to be solved by the invention
The invention aims to solve the problems of complex preparation process, high cost and low yield of the existing 3-alkoxy acrylic ester.
2. Technical proposal
In order to achieve the above purpose, the technical scheme provided by the invention is as follows:
The invention relates to a preparation method of 3-alkoxy acrylic ester, which comprises the steps of introducing carbon monoxide into metal alkoxide solution of ester, and preserving heat until the reaction is complete; and then evaporating excessive ester, dripping an alcohol solution of hydrogen chloride, carrying out heat preservation reaction completely, carrying out aftertreatment to obtain 3, 3-dialkoxy propionate, adding a catalyst, carrying out cracking reaction, and carrying out reduced pressure distillation to obtain the 3-alkoxy acrylate.
Preferably, the ester is an ester with alpha-H, and is any one of methyl acetate, ethyl acetate, propyl acetate and butyl acetate, the metal alkoxide is any one of sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, magnesium ethoxide and tert-butanol, and the alcohol is any one of methanol, ethanol, propanol and butanol.
Preferably, the method specifically comprises the following steps:
s100, mixing materials, and adding a metal alkoxide mixed solution of the ester into a high-pressure reaction kettle;
S200, carrying out primary reaction, introducing carbon monoxide into a high-pressure reaction kettle, and heating for reaction;
s300, carrying out primary distillation, transferring the feed liquid after primary reaction into a distillation kettle for distillation, and evaporating and removing excessive ester;
S400, carrying out secondary reaction, namely slowly dropwise adding a 10% hydrogen chloride alcohol solution into the feed liquid after primary distillation to carry out secondary reaction;
S500, post-treatment, namely adding a PH value regulator into the feed liquid after the secondary reaction, regulating the PH value of the feed liquid to 7-8, and performing centrifugal operation after PH regulation is finished to separate out salt;
S600, performing secondary distillation, namely heating, distilling and concentrating the feed liquid obtained by post-treatment to obtain the required 3, 3-dialkoxypropionate;
S700, cracking reaction, namely adding a catalyst into 3, 3-dialkoxy propionate, and performing cracking reaction at the temperature of 120-150 ℃ for 6-8 hours;
s800, performing reduced pressure distillation, namely performing reduced pressure distillation on the feed liquid obtained in the step S700 to obtain the 3-alkoxy acrylate.
Preferably, the molar ratio of ester to metal alkoxide in step S100 is 1: 1-20: 1.
Preferably, carbon monoxide is introduced in the step S200, the reaction pressure is controlled to be 2-4 Mpa, and the reaction temperature is controlled to be 40-70 ℃.
Preferably, the distillation temperature in the step S300 is 60 to 80 ℃, and the distillation completion determination condition is that the condensation tube lasts for 5 minutes or more without precipitating esters.
Preferably, the molar ratio of hydrogen chloride in the dropwise added hydrogen chloride methanol solution in the step S400 to the metal alkoxide in the step S100 is 1: 1-2: 1.
Preferably, the PH regulator in the step S500 is specifically any one of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium methoxide, potassium methoxide, sodium tert-butoxide, and potassium tert-butoxide, and after the PH regulation is completed, the centrifugation is performed to separate out the salt, and the centrifugation speed is 1000r/min to 2000r/min.
Preferably, the distillation temperature in the step S600 is 60-80 ℃ and the distillation time is 7-8 h.
Preferably, the catalyst added in the step S700 is specifically p-toluenesulfonic acid, sodium bisulfate or potassium bisulfate, the addition amount of the catalyst is 1-5% of the mass of 3, 3-dimethoxy propionate, the distillation temperature of the reduced pressure distillation in the step S800 is 60-80 ℃, and the distillation time is 7-8 h.
3. Advantageous effects
Compared with the prior art, the technical scheme provided by the invention has the following beneficial effects:
The invention relates to a preparation method of 3-alkoxy acrylic ester, which comprises the steps of introducing carbon monoxide into metal alkoxide solution of ester, and preserving heat until the reaction is complete; then evaporating excessive ester, dripping alcohol solution of hydrogen chloride, after heat preservation reaction is completed, obtaining 3, 3-dialkoxy propionate through aftertreatment, then adding catalyst, and obtaining 3-alkoxy acrylate through reduced pressure distillation after cracking reaction.
Drawings
FIG. 1 is a flow chart of a method for preparing 3-alkoxy acrylate according to the present invention.
Detailed Description
In order that the invention may be readily understood, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings, in which, however, the invention may be embodied in many different forms and are not limited to the embodiments described herein, but are instead provided for the purpose of providing a more thorough and complete disclosure of the invention.
It will be understood that when an element is referred to as being "mounted" on another element, it can be directly on the other element or intervening elements may also be present; when an element is referred to as being "connected" to another element, it can be directly connected to the other element or intervening elements may also be present; the terms "vertical," "horizontal," "left," "right," and the like are used herein for illustrative purposes only.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs; the terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention; the term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
Example 1
Referring to FIG. 1, in the preparation method of 3-alkoxy acrylate in this example, 100.0g of methyl acetate and 16.5g of sodium methoxide are put into a high-pressure reaction kettle, then CO gas is introduced to 4.0MPa, the reaction temperature is 60 ℃ and the CO pressure is controlled to be 4.0MPa, and after the reaction is finished, the feed liquid is transferred into a distillation kettle to evaporate excessive methyl acetate. Slowly dripping 131.4g of 10% hydrogen chloride methanol solution, controlling the reaction temperature to 40 ℃, performing post-treatment, concentrating, adding 0.8g of p-toluenesulfonic acid into the concentrated solution, cracking for 6 hours at 120-150 ℃, and finally performing reduced pressure rectification to obtain the 3-methoxy methyl acrylate with 27.1g, the purity of 99.2% and the yield of 77.5%. Under the action of strong alkali sodium alkoxide, methyl acetate makes alpha carbon on methyl acetate form carbanion, and then forms sodium enolate after being combined with carbon monoxide and rearranged. The enol sodium salt and methanol respectively perform addition and substitution reaction in the presence of hydrogen chloride to generate 3, 3-dimethoxy methyl propionate. The method has the advantages of few reaction steps, simple operation and high yield, does not introduce a third-party solvent, and can recycle redundant raw material methyl acetate, thereby further saving the cost.
Example 2
Referring to FIG. 1, in the preparation method of 3-alkoxy acrylate in this example, 200.0g of methyl acetate and 16.5g of sodium methoxide are put into a high-pressure reaction kettle, then CO gas is introduced to 3.5MPa, the reaction temperature is 50 ℃, the CO pressure is controlled to be 2.8-3.2MPa, and after the reaction is finished, the feed liquid is transferred to a distillation kettle to evaporate excessive methyl acetate. Slowly dropwise adding 109.3g of 10% hydrogen chloride methanol solution at the reaction temperature of 50 ℃, carrying out aftertreatment, concentrating, adding 1.8g of sodium bisulfate into the concentrated solution, cracking for 6 hours at 120-150 ℃, and finally carrying out reduced pressure rectification to obtain the 3-methoxy methyl acrylate with 25.6g, the purity of 98.9% and the yield of 73.0%.
Example 3
Referring to FIG. 1, in the preparation method of 3-alkoxy acrylate in this example, 300.0g of methyl acetate and 16.5g of sodium methoxide are put into a high-pressure reaction kettle, then CO gas is introduced to 3MPa, the reaction temperature is 50 ℃, the CO pressure is controlled to be 2.8-3.2MPa, and after the reaction is finished, the feed liquid is transferred to a distillation kettle to evaporate excessive methyl acetate. Slowly dripping 131.4g of 10% hydrogen chloride methanol solution at 45 ℃, performing post-treatment, concentrating, adding 1.3g of potassium hydrogen sulfate into the concentrated solution, cracking for 6 hours at 120-150 ℃, and finally performing reduced pressure rectification to obtain the 3-methoxy methyl acrylate with 29.2g, the purity of 99.5% and the yield of 83.7%.
Example 4
Referring to FIG. 1, in the preparation method of 3-alkoxy acrylate in this example, 400.0g of methyl acetate and 16.5g of sodium methoxide are put into a high-pressure reaction kettle, CO gas is introduced to 3.5MPa, the reaction temperature is 60 ℃, the CO pressure is controlled to be 3.5MPa, and after the reaction is finished, the feed liquid is transferred to a distillation kettle to evaporate excessive methyl acetate. Slowly dripping 163.4g of 10% hydrogen chloride methanol solution at the reaction temperature of 55 ℃, carrying out aftertreatment, concentrating, adding 2.0g of p-toluenesulfonic acid into the concentrated solution, cracking for 6 hours at 120-150 ℃, and finally decompressing and rectifying to obtain the 3-methoxy methyl acrylate with 28.0g, the purity of 98.8% and the yield of 79.6%.
Example 5
Referring to FIG. 1, in the method for preparing 3, 3-dialkoxypropionate of this example, 300.0g of ethyl acetate and 20.8g of sodium ethoxide are put into a high-pressure reaction kettle, CO gas is introduced to 3.5MPa, the reaction temperature is 60 ℃, the CO pressure is controlled to be 3.5MPa, and after the reaction is finished, the feed liquid is transferred to the distillation kettle to evaporate excessive ethyl acetate. Slowly dripping 163.4g of 10% hydrogen chloride ethanol solution, controlling the reaction temperature to be 55 ℃, performing aftertreatment, concentrating, distilling, adding 2.1g of p-toluenesulfonic acid into the concentrated solution, cracking for 6 hours at 120-150 ℃, and finally performing reduced pressure rectification to obtain the 3-ethoxyethyl acrylate, wherein the purity is 98.5%, and the yield is 66.1%.
Comparative example one
In the preparation method of the 3-alkoxy acrylic ester in the comparative example, 300.0g of methyl acetate and 16.5g of sodium methoxide are put into a high-pressure reaction kettle, CO gas is introduced to 0.2MPa, the reaction temperature is 60 ℃, the CO pressure is controlled to be 0.2MPa, and after the reaction is finished, the feed liquid is transferred to a distillation kettle to evaporate excessive methyl acetate. Slowly dripping 131.4g of 10% hydrogen chloride methanol solution at 45 ℃, performing post-treatment, concentrating, adding 0.9g of p-toluenesulfonic acid into the concentrated solution, cracking for 6h at 120-150 ℃, and finally performing reduced pressure rectification to obtain the 3-methoxy methyl acrylate with 20.5g, the purity of 99.2% and the yield of 58.7%.
Comparative example two
In the preparation method of the 3-alkoxy acrylic ester in the comparative example, 300.0g of methyl acetate and 16.5g of sodium methoxide are put into a high-pressure reaction kettle, CO gas is introduced to 3.0MPa, the reaction temperature is 80 ℃, the CO pressure is controlled to be 3.0MPa, and after the reaction is finished, the feed liquid is transferred to a distillation kettle to evaporate excessive methyl acetate. Slowly dripping 131.4g of 10% hydrogen chloride methanol solution at 45 ℃, performing post-treatment, concentrating, adding 1.4g of sodium bisulfate into the concentrated solution, cracking for 6 hours at 120-150 ℃, and finally performing reduced pressure rectification to obtain the 3-methoxy methyl acrylate with 24.4g, the purity of 99.6% and the yield of 69.9%.
Comparative example three
In the preparation method of the 3-alkoxy acrylic ester in the comparative example, 300.0g of methyl acetate and 16.5g of sodium methoxide are put into a high-pressure reaction kettle, CO gas is introduced to 3.0MPa, the reaction temperature is 60 ℃, the CO pressure is controlled to be 3.0MPa, and after the reaction is finished, the feed liquid is transferred to a distillation kettle to evaporate excessive methyl acetate. Slowly dripping 131.4g of 10% hydrogen chloride methanol solution at 65 ℃, performing post-treatment, concentrating, adding 0.9g of potassium hydrogen sulfate into the concentrated solution, cracking for 6 hours at 120-150 ℃, and finally performing reduced pressure rectification to obtain the 3-methoxy methyl acrylate with 20.9g, the purity of 99.1% and the yield of 59.6%.
In conclusion, the preparation method of the 3-alkoxy acrylic ester has the advantages of few reaction steps, simple operation, high yield, no introduction of a third-party solvent, recycling of redundant raw material methyl acetate and further cost saving.
The foregoing examples merely illustrate certain embodiments of the invention and are described in more detail and are not to be construed as limiting the scope of the invention; it should be noted that it is possible for a person skilled in the art to make several variants and modifications without departing from the concept of the invention, all of which fall within the scope of protection of the invention; accordingly, the scope of protection of the present invention is to be determined by the appended claims.

Claims (4)

1. A preparation method of 3-alkoxy acrylic ester is characterized in that: introducing carbon monoxide into an ester metal alkoxide solution, and preserving heat until the reaction is complete; then evaporating excessive ester, dripping an alcohol solution of hydrogen chloride, carrying out heat preservation reaction completely, then carrying out aftertreatment to obtain 3, 3-dialkoxy propionate, adding a catalyst, carrying out cracking reaction, and carrying out reduced pressure distillation to obtain 3-alkoxy acrylate; the method specifically comprises the following steps:
s100, mixing materials, and adding a metal alkoxide mixed solution of the ester into a high-pressure reaction kettle; the molar ratio of ester to metal alkoxide in step S100 is 1: 1-20: 1, a step of;
S200, carrying out primary reaction, introducing carbon monoxide into a high-pressure reaction kettle, and heating for reaction; introducing carbon monoxide in the step S200, controlling the reaction pressure to be 2-4 Mpa, and controlling the reaction temperature to be 40-70 ℃;
S300, carrying out primary distillation, transferring the feed liquid after primary reaction into a distillation kettle for distillation, and evaporating and removing excessive ester; the distillation temperature in the step S300 is 60-80 ℃, and the distillation completion judging condition is that no ester is separated out after the condensing tube lasts for more than 5 minutes;
S400, carrying out secondary reaction, namely slowly dropwise adding a 10% hydrogen chloride alcohol solution into the feed liquid after primary distillation to carry out secondary reaction; the molar ratio of the hydrogen chloride in the dropwise added hydrogen chloride alcohol solution in the step S400 to the metal alkoxide in the step S100 is 1: 1-2: 1, a step of;
S500, post-treatment, namely adding a PH value regulator into the feed liquid after the secondary reaction, regulating the PH value of the feed liquid to 7-8, and performing centrifugal operation after PH regulation is finished to separate out salt;
S600, performing secondary distillation, namely heating, distilling and concentrating the feed liquid obtained by post-treatment to obtain the required 3, 3-dialkoxypropionate;
S700, cracking reaction, namely adding a catalyst into 3, 3-dialkoxy propionate, and performing cracking reaction at the temperature of 120-150 ℃ for 6-8 hours; the catalyst added in the step S700 is specifically p-toluenesulfonic acid, sodium bisulfate or potassium bisulfate, the addition amount of the catalyst is 1-5% of the mass of 3, 3-dimethoxy propionate, the distillation temperature of the reduced pressure distillation in the step S800 is 60-80 ℃, and the distillation time is 7-8 h;
s800, performing reduced pressure distillation, namely performing reduced pressure distillation on the feed liquid obtained in the step S700 to obtain the 3-alkoxy acrylate.
2. The method for preparing 3-alkoxy acrylate according to claim 1, wherein: the ester is any one of methyl acetate, ethyl acetate, propyl acetate and butyl acetate, the metal alkoxide is any one of sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, magnesium ethoxide and potassium tert-butoxide, and the alcohol is any one of methanol, ethanol, propanol and butanol.
3. The method for preparing 3-alkoxy acrylate according to claim 1, wherein: the PH value regulator in the step S500 is specifically any one of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium methoxide, potassium methoxide, sodium tert-butoxide and potassium tert-butoxide, and after PH regulation, centrifugal operation is performed to separate out salt, wherein the centrifugal rotation speed is 1000 r/min-2000 r/min.
4. The method for preparing 3-alkoxy acrylate according to claim 1, wherein: the distillation temperature in the step S600 is 60-80 ℃, and the distillation time is 7-8 h.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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CN103113227A (en) * 2013-02-27 2013-05-22 湖南海利化工股份有限公司 Preparation method of 3-methyl methoxyacrylate
CN103965042A (en) * 2014-05-09 2014-08-06 浙江同丰医药化工有限公司 Synthetic method of ethyl ethoxy acrylate
CN104058960A (en) * 2014-06-27 2014-09-24 湖南海利化工股份有限公司 Preparation method of methyl 3-methoxyacrylate
CN104822651A (en) * 2012-11-26 2015-08-05 巴斯夫欧洲公司 Method for producing methyl formate by reacting methanol with carbon monoxide in presence of catalyst system which comprises alkali formate and alkali alcoholate
CN105037151A (en) * 2015-05-29 2015-11-11 南京工业大学 Preparation method of 3-alkoxy alkyl propionate
CN105418421A (en) * 2015-10-23 2016-03-23 吴清来 Synthesizing method for 3-methoxyacrylate
CN107879936A (en) * 2017-12-05 2018-04-06 淄博益利化工新材料有限公司 A kind of preparation technology of 3 methoxy-methyl acrylate
CN109438237A (en) * 2018-12-12 2019-03-08 浙江华方药业股份有限公司 A kind of preparation method of 3- ethoxy ethyl acrylate
CN111153799A (en) * 2020-01-20 2020-05-15 浙江本立科技股份有限公司 Preparation method of methyl 3-methoxyacrylate

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102746156A (en) * 2012-05-31 2012-10-24 上海海事大学 Production technology of methyl 3-methoxyacrylate
CN104822651A (en) * 2012-11-26 2015-08-05 巴斯夫欧洲公司 Method for producing methyl formate by reacting methanol with carbon monoxide in presence of catalyst system which comprises alkali formate and alkali alcoholate
CN103113227A (en) * 2013-02-27 2013-05-22 湖南海利化工股份有限公司 Preparation method of 3-methyl methoxyacrylate
CN103965042A (en) * 2014-05-09 2014-08-06 浙江同丰医药化工有限公司 Synthetic method of ethyl ethoxy acrylate
CN104058960A (en) * 2014-06-27 2014-09-24 湖南海利化工股份有限公司 Preparation method of methyl 3-methoxyacrylate
CN105037151A (en) * 2015-05-29 2015-11-11 南京工业大学 Preparation method of 3-alkoxy alkyl propionate
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CN107879936A (en) * 2017-12-05 2018-04-06 淄博益利化工新材料有限公司 A kind of preparation technology of 3 methoxy-methyl acrylate
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